


Why’s It Feel So Good?

by tricia_16



Series: I’d Do It Over and Over and Over Again [1]
Category: Supernatural
Genre: Dean Winchester is Not Heterosexual, Destiel endgame, F/M, Frottage, M/M, Multi, Oral Sex, SPOILER:, Threesome - F/M/M, Unsafe Sex, Vaginal Fingering, Vaginal Sex
Language: English
Status: Completed
Published: 2019-07-11
Updated: 2019-07-11
Packaged: 2020-06-26 02:38:55
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 9,175
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19758889
Author URL: https://archiveofourown.org/users/tricia_16/pseuds/tricia_16
Summary: In a desperate attempt to save his dying relationship with Lisa, Dean Winchester agrees to invite another man into their bedroom. He’s always considered himself to be completely straight... so why does being with this Cas guy feelso good?





	Why’s It Feel So Good?

**Author's Note:**

> **_2014_ **

“Are you sure you wanna do this, Lis?” Dean checks.

“I’m sure.” Her smile is easy, reassuring. Gorgeous. Something he hasn’t seen enough of for a long time. “Are you only asking because _you’re_ not sure?”

Truthfully, his stomach's been in knots since he agreed to do this. Even now, only minutes away from a knock on their door, his hands are clammy and his heart’s beating way too fast to be normal. “Be like watching live porn, right? ‘cept my girl’s way hotter than anybody on PornHub.”

She rolls her eyes as she moves towards the fridge, but there’s a fondness there that makes his chest ache. It’s that _longing_ that he’s been feeling for a while now. The longing for things to finally go back to how it used to be when their relationship was easy and fun. 

He loves Lisa more than he’s ever loved anybody, and the sex is great. Really great. Hell, they’d had sex yesterday and he's raring to go again. He really doesn’t have anything to complain about... except maybe sometimes he feels like he’s just going through the motions of working, coming home, cooking, cleaning, and going to bed all with Lisa in the background instead of by his side. Not that they need to be attached 24/7 or anything, but he feels lonely a lot even though she’s there, and a tiny part of him wonders how normal that is. Does everybody feel like that in their relationships? He didn’t at first but it’s happening more and more frequently now. Lisa noticed he hasn’t been as happy as he used to be, and when he tried to explain the lonely thing, they tried several things to make it better. After date nights, paint nights, nights out at the club, sex toys and role play didn’t seem to make much of a difference, they decided to give a threesome a shot.

Alcohol may have been involved in the decision making process. 

A part of him still thinks this is crazy. What does it say about them that his girlfriend of almost two years wants to fuck somebody else? Sure, Lisa’s told him a million times it’s less about that and more about having him watch her with somebody else, and it’s not like that’s an unappealing thought. He’s seen her dance at the club with other guys, seen how hot she is with them. He’s seen the way she shakes her head and points at him when the guy she’s dancing with gets too handsy. He always peacocks over their groans of jealousy, feeling hot and powerful knowing he has what somebody else wants, and that one time, they barely made it to the Impala before Lisa was riding him in the back seat. 

So he knows the _idea_ of Lisa with somebody else is hot for both of them. But the idea of another man in their home? In their bed? _Naked_ in their bed?

He feels that weird prickly sensation on his skin again, like it’s too tight for his body or something, but thankfully, that’s when Lisa hands him a beer. “Cas is a really nice guy. You’re gonna love him.”

“Just as long as _you_ don’t love him,” Dean says, twisting off the cap.

She actually laughs at that, and after Dean raises his eyebrows in a silent question, she elaborates while he gulps greedily from his beer. “I already told you all of this. He’s easy on the eyes, but I’ve known him for years, and as nice as he is, he’s a little out there for me.”

Dean’s voice is dripping with sarcasm when he replies, “Wow, I can’t wait to have _that_ rolling around in our bed.”

“He’s _nice,”_ she insists. “I’m just not stupid enough to fall for a guy who’s about to move to another country to minor in bees.”

“Bees?” Dean repeats, sure he isn’t hearing her right. “How do you minor in something the size of a nickel?” Then, he smirks. “Guess it’s too small to be a major.”

Lisa laughs while he takes another drink from the bottle. He leans into it when he feels her fingers stroke through his hair, her long nails catching on his scalp in a pleasant way. “It’s good to hear you laugh, babe. See, this is working already.”

“I’m hotter than him, right?” It was a joke, meant to carry on the lightheartedness of the conversation, but when she hesitates, his jaw drops. “Hey!”

She laughs him off. “You’re both attractive in different ways. You’re like, model hot,” she says, something she’s said a lot over the last few years. “And he’s got the rugged, tall, dark, and handsome thing going on.” He narrows his eyes at her. “But I’d obviously pick you eleven out of ten times.”

She says it while batting her eyelashes and twirling a lock of her long, dark hair around her finger, clearly placating him, and still, he feels better for it. He finishes off his beer and places the bottle on the end table next to the couch before he hauls her into his lap. She’s looking especially hot tonight with her hair down loose and wavy, some smokey cat eye thing going on, and a yellow shirt that ties up behind her neck showcasing how she’s clearly not wearing a bra underneath. 

She giggles seductively and rearranges herself so she’s more comfortable straddling him. Dean runs his hands over the tight denim stretching over her athletic thighs and she hums quietly. “Can’t even wait the two minutes until he gets here?” she teases.

“Just wanna make sure you’re really, really ready,” he says back, shooting her a patented Dean Winchester million watt smile. 

When she leans in to kiss him, it’s his turn to hum quietly. Her lips are soft and familiar, and it’s easy to do just what he knows she likes: to run his hands through her hair to keep it out of her face, to nudge her lips open with his and sink into the silky heat of her mouth. His fingers brush her bare back and he feels his dick slowly beginning to fill. She slides her tongue into his mouth and flicks the tip of it against his while his hands skirt down her back to settle onto her hips, comforted by the softness beneath his palms. 

Lisa’s _beautiful._ She’s got all the right curves in all the right places, she's not rail thin like some other girls, and she’s got a hell of a sexual appetite. In fact, she might like sex more than he does. She definitely initiates a big portion of the time, and even though he might not always be in the mood, it never takes him long to get there once she’s on top of him. She’s hands-down the most demanding woman he’s ever been with in bed, and she’d even been the first to help him figure out just how into that he was. She’s doing it now, even. Her hands press into his shoulders, pushing him back further into the couch, and she takes control of the kiss with her lips sealed more firmly against his.

Arousal jolts through him in a pleasing hum, and he turns to putty under her hands. She starts rocking her hips slowly and _fuck yes._ Two years together and feeling the weight of her—not substantial or anything, but _enough—_ on top of him still has his blood racing south.

Unfortunately for him, that’s when there’s a knock on the door.

He groans into her mouth, and she’s smiling knowingly when she gets to her feet, holding out a hand for him. 

“What?” he says, allowing himself to be pulled up.

“We have to meet him at the door.”

He pointedly glances down at where his dick is making his hard-on obvious along his leg (damn skinny jeans) and makes a quick attempt at tucking it up into the waistband instead. He looks back at Lisa only to see her eyes trained on the bulge on his pants with her teeth digging into her bottom lip. “Not helping,” he says quietly.

She’s giggling when she turns to pull the door open. “Hey, Cas.”

“Lisa.”

He can’t see past her right away, but his eyebrows rise unintentionally when he hears how low this guy’s voice is. 

“Come on in,” she says, stepping away from the door.

And there he is. Tall, dark, and handsome fits, but he doesn’t really get the rugged thing. Yeah, he's got a thin layer of scruff on his face, but if it wasn’t for the mop of disheveled hair, he’d also be screaming nerd. Which, with the button down shirt and fucking _loafers_ on his feet, he’s pretty damn close to anyway. But Dean’s not blind, and he's man enough to admit he can see the appeal of a strong jaw, straight nose, and eyes as blue as the sky, even if they are all on a dude (though this guy's no Harrison Ford).

He can also see the way the guy sweeps his eyes up and down Dean's body, stopping for a few seconds too long to linger on his face—specifically on his lips. Jesus, Cas even does the same teeth digging into his bottom lip thing as Lisa was doing only a second before, and considering Cas is a dude and aiming that look at him without any attempt to hide it, it’s... it’s, well... it's fucking _lewd_ to be looking at another guy like that in his own damn living room! It makes his ears feel too warm and he knows he’s blushing and he’s about to say _something,_ but then Cas steps forward, offering his hand to shake. 

Dean spares Lisa a quick _what the fuck_ look about the dude who looks at him like he wants to eat him alive one second and then shakes his hand the next, but clasps Cas’s hand with his, his eyes automatically dropping down to the hand so big it basically swallows his. Dean’s a big guy so finding somebody with bigger hands than him is unusual, and a surprising, electric feeling shoots through him. For reasons he doesn’t understand, he has to will away the blush he can feel threatening to crawl from his ears across his cheeks. 

“I’m Dean.”

“Castiel, but Cas is fine.”

Dean takes his hand back, pretending his stomach isn’t doing some weird flippy thing due to nerves (and maybe because of how surprisingly firm that handshake had been). 

“So you wanna fuck my girlfriend, huh?” Dean says, trying to break the ice.

“Yes.”

He huffs out a laugh at the dry response at the same time Lisa smiles at Cas flirtatiously. She also runs her hand down Dean’s arm, though, and then links their fingers together. “Do you want a drink first? Dean just finished a beer and I have a bottle of wine open in the fridge.”

“No, thank you.”

“Follow us, then,” Lisa says, turning around to start walking toward the bedroom. Both he and Cas wait just a second, their eyes falling to watch her hips sway as she walks. She shoots a smile over her shoulder, catching them both, and Dean smiles wide before he remembers the dude next to him. 

He casts his gaze Cas’s way to see what he says about getting caught. “You’re a very lucky man,” Cas comments. “And just so we’re clear, Lisa is a very attractive woman but she’s not my type outside of the bedroom.”

 _Not my type_ rubs him the wrong way considering he's talking about his girlfriend. “What’s that supposed to mean?”

Cas cocks his head to the side, a little crease appearing between his eyebrows. “I’m just saying that I’m attracted to her purely on a physical level.” 

“Oh,” Dean says lamely. “Well, she’s the one who's into this, so have at ‘er, I guess.”

“After you,” Cas says, gesturing to the hallway.

Whatever. He walks down the hall to the bedroom, practically feeling Cas’s eyes on him. If his read on how Cas was looking at his lips earlier was right, the dude’s probably checking out his ass the same way he was Lisa’s a minute ago, and he has no idea what’s worse. 

He steps into his bedroom feeling all kinds of weird, wondering how the hell you go about having a threesome with your girlfriend and another guy, but he doesn’t have much time to think about it because Lisa is waiting for him. He barely gets into their room before she’s pulling him down into a kiss by the back of his neck with one hand, backing him up against the wall, and slipping her other hand down, down, down until she’s rubbing over his dick through his jeans. 

His eyes stay open for a second longer than usual, hyper-aware of Cas watching them, but then Lisa’s fingers start working on his fly and the thrill of anticipation has his eyes drifting closed. He forgets all about Cas once Lisa gets her hand in his pants, and he just gives into the way she’s rocking her hips and hand against him, her mouth taking him apart with calculated flicks of her tongue they both know drives him crazy. 

She moans against his lips at the same time the light behind his eyelids changes, and he opens his eyes again to see that Cas has moved Lisa’s hair off of one shoulder and is currently kissing his way along the side of her neck. Heat punches into him like a fist to the gut, and his fingers tighten on Lisa’s hips. Cas’s eyes flick up to him, so fucking blue, and they hold eye contact while Cas presses soft kisses along Lisa’s jaw towards her mouth—which Dean is currently having a hard time remembering to kiss.

After a fleeting smile aimed at Dean, Lisa turns her head and meets Cas’s lips for their first kiss. He’s stunned stupid watching the lips of his girlfriend moving along with somebody else’s. Is this what it looks like when she kisses him? No, he decides after another few seconds. She seems more timid with Cas, unsure in a way she never is with him, and while it’s kind of exciting to watch them figure it out, that’s when she turns around completely and suddenly he’s got her ass nudging against his dick.

God, Lisa’s got an unbelievable ass. He’s enjoying the show and the sporadic pressure with his hands back on her hips when he feels much larger hands land on his. As a surge of excitement runs through him, Cas urges Lisa to rock back against him, and the friction on his burgeoning erection has him exhaling sharply. Lisa moans and starts rolling her hips with the rhythm Cas set, and Dean pulls his hands away from Cas's to move Lisa's hair out of the way so he can kiss her soft skin. With his mouth seeking out the places on her neck and behind her ear he knows she likes, he slips his hands over her soft stomach and up towards her chest. 

He brushes his thumbs over her nipples and feels her breath hitch at the same time the sensitive flesh springs to life beneath his hands. That’s a green light if there ever was one, and so he cups her breasts in his hands and squeezes gently, feeling desire zing through him at the familiar weight in his hands. 

Her head falls back on his shoulder and she breathes, “Fuck, this is hot.” She kisses under his chin when he chuckles lightly, and then Cas’s hair is tickling his face as he starts mouthing at the bend of her neck, slowly moving down her throat and between her breasts. Big, nimble fingers appear between the back of Lisa’s neck and his shoulder, and then Cas is untying her shirt and the front falls down. Dean moves his hands out of the way so he can get two handfuls of Lisa’s naked flesh, immediately rolling her nipples between his fingers and dragging his cock against her ass more eagerly. 

He makes a sound of surprise when wet heat encircles his fingers and Lisa’s left nipple, and he looks over her shoulder to see Cas sealing his mouth over both. Lisa’s moan muffles his own as Cas’s tongue licks over the pad of his thumb, and he has about three seconds to wonder if it’s weird that he’s turned on by that (and the scratch of Cas’s facial hair on his knuckles) before Cas’s eyes find his again and then it doesn’t matter because his mind goes completely blank as his insides catch on fire. 

The spell breaks when Cas starts pulling down Lisa’s top over her hips, his mouth moving down the middle of her stomach and over her belly button. Dean feels his cock twitch at the sight of a wet trail on Lisa’s skin put there by somebody else, at Cas’s fingers flipping the button on her fly, at Cas’s giant fucking hands pushing her jeans down her legs with his palms skirting along her skin as he goes.

Lisa turns around again once her jeans are pulled over her feet, and then she’s pushing _him_ towards the bed. She lifts his t-shirt over his head and as the backs of his knees hit the mattress, she grins and pushes him back. He falls onto his back and Lisa straddles him the way she has a thousand times before, looking sexy as hell now that she's in control. 

“He likes it a little rough,” Lisa says to Cas.

“Noted.” 

He’s quickly discovering that Cas’s voice is exactly the kind of rough he had no idea he’s into. It’s lower now than it was before, and he wonders idly if Cas sounds like that when he’s turned on, then tries not to wonder why the idea makes his cock feel harder than it’s ever been. He only notices Cas has lost his shirt and jeans somewhere along the way when Cas takes his place behind Lisa because he’s suddenly distracted by the significant bulge of Cas’s biceps where they wrap around Lisa from behind, and how incredibly thick his thighs are where they’re bracketing Lisa’s. 

Then those massive hands are on Lisa’s tits and her head is tilted back, her hips grinding down on Dean’s cock through his jeans and probably back against Cas at the same time. Since Cas is busy with her breasts, he keeps his eyes trained on another man’s hands on his girlfriend and slips two fingers into her panties, listening to her gasp with pleasure. 

He smirks to himself, because yeah, this is something he can do. He knows Lisa like the back of his hand and he knows just how to tease her until she loses her cool and takes control again by rubbing herself against his fingers. But his cocky smile falters when Cas’s hand covers his, and then Lisa is cursing a breathy, “Oh God,” as one of Cas’s fingers slots between his and Lisa has three fingers moving over her slickened sex. 

Cas’s eyes catch his again and the fucker winks, causing Dean’s face to turn red right to his ears. 

It shouldn’t be this hot to show another man exactly how to get Lisa off, but Cas is following his lead and keeping eye contact and Dean’s already breathing so hard he’s panting. Cas’s cheeks are tinged pink and he’s chewing on his bottom lip looking like he wants to eat him alive, and jesus, there’s something _magnetic_ about him and he can’t tear his eyes away. 

“Dean,” Lisa prompts, and even with his scrambled brains he knows just what she wants.

He slides a finger inside of her and she smiles with relief, but catches him off guard by pushing up so she’s hovering over top of him, pulling his hand up with her. She braces herself with one hand on his chest, the other one still holding his wrist, and his eyes are drawn to her hanging breasts. He uses the opportunity to seek out one of her nipples. He sucks it into his mouth and swirls his tongue around, using the easy access position of her lifted hips to add a second finger at the same time. 

“Yeah, babe, you know what I like,” Lisa breathes, and he feels smug for three seconds until he jerks back onto the pillow with surprise when rough fingers curl under the elastic band of his boxers. 

Considering Lisa’s hands are busy he knows it’s Cas, and his cock is inexplicably _throbbing_ when he lifts his hips to let Cas pull off his jeans and boxers all in one go. 

“Christ,” Cas curses, running his hands back up Dean’s thighs and making his insides feel like jelly. “Your boyfriend’s hung like a horse.”

All kinds of alarms are going off in his mind, his face hotter than it’s ever been. _Cas is looking at his cock!_ _Cas is looking at his cock! Cas is looking at his cock!_

“I know,” Lisa smiles. 

Through his panic, he's distantly aware of Cas’s hands leaving his thighs, another pair of boxers hitting the floor, of Cas’s fingers pulling off Lisa’s underwear, and then Lisa saying, “Hold him steady for me, Cas.” 

“Gladly.”

And then _holy fucking shit_ another guy’s hand is wrapping around his cock. Cas’s hand is big, rough, calloused maybe, and sparks of pleasure explode along his spine. Cas’s confident touch is nothing like the soft hands and unsure grip of any woman he’s ever been with, and Dean’s body works on auto drive. 

He thrusts up into Cas’s firm grasp, and a strangled, _“Fuck,”_ is pulled from his throat as Cas pumps him in his hand, once, twice. A thumb runs along his cockhead and apparently he’s fucking dripping because he can feel the slick fluid smear along his slit and another stifled sound escapes him. 

“You like that baby?” Lisa whispers and Dean doesn’t even get a chance to lie before she’s lowering herself onto him and hot, wet heat engulfs him all at once. 

Cas’s hand is still between them, but he flips his hand over palm up. Dean’s cock is trapped in the vee of Cas’s fingers, and as he’s thinking about how the extra stimulation is fucking _amazing,_ he feels Cas’s knuckles brush his skin at the same time Lisa groans. His skin might actually be on fire with how turned on he is right now. He knows Cas—another guy—is massaging Lisa’s clit and she’s fucking loving it, evidenced by how she starts rocking on top of him, and the tight squeeze of her walls around his thick cock is indescribably good. 

Just when he thinks that’s all he can handle, Lisa leans down so she can kiss him. She makes a quiet little sound of pleasure against his mouth and his mind starts going in a million different directions. Unbearable heat is already racing through his veins and he’s afraid he’s going to embarrass himself by coming way too soon, but that’s when Lisa giggles as she’s lifted right off of him. She lands with a whoosh on her back on the mattress beside him, and when he expects Cas to occupy the space between Lisa’s legs, it’s actually him who Cas drapes himself over. 

Dean’s eyes are wide as saucers for a split second before he feels the weirdly smooth but hard length of Cas’s cock slot alongside his, and then his jaw falls open and a garbled sound is ripped out of him when Cas’s heavy weight and sharp hip bones pin him to the mattress. 

He can’t even _breathe_ through how good this feels. Jesus christ. He’s gonna come. He’s gonna blow his load all over Cas and he’s never gonna be able to look him in the face ever again, and that’s a damn shame in itself because the guy’s got one hell of a face. 

But that’s when he hears a wet sound that distracts him, pulls his attention to Lisa, only to find her watching the two of them hungrily while she works her clit. 

“You guys are hot together,” she says breathily. “Kiss me.”

He meets her halfway when she leans in, and as their lips come together, Cas rocks against him. Their cocks pressing against one another and between their bodies at the same time is fucking _hot,_ and that’s before Cas starts working on the exposed line of his throat. Once again, the brand-new feeling of stubble scratching his skin is exciting and he’s into it in a way he never expected himself to be... and apparently that sound he hears is himself... _moaning?_

He’s never been super noisy in bed but obviously he hasn’t been doing it right because the pleasure he feels from having Cas on top of him and knowing Lisa’s playing with herself next to him is unlike anything he’s ever felt and it only makes him want _more._

He has no recollection of moving it there, but his hand is squeezing Cas’s bicep and _fuck_ he’s solid. Strong. Dean’s one hand moves from Cas’s bicep to his shoulder and down his firm back, his pulse racing when he feels the flex of firm muscles as Cas rolls his hips against him. 

Lisa breaks the seal of their lips long enough to say, “C’mere, Cas,” and then—after one more dirty grind of Cas’s hips against Dean’s aching erection that has him seeing stars—Cas positions himself on top of Lisa instead. 

Only then does his brain kick back into gear, and before he’s given it any thought at all, he hears himself say, “I’m not gay.”

Cas and Lisa both stop whatever they were doing to turn to face him. Cas’s face cracks on a huge, cocky smile, like him saying that is the funniest fucking thing he’s ever heard, but Lisa gives Cas’s shoulder a nudge and his lips quirk once more before he buries his face in Lisa’s neck. 

“We know, babe,” she says, laughing slightly like even the idea is funny to her. “Cas just thinks you’re hot and can’t keep his hands off you. Not that I can blame him.”

Cas makes a quiet sound of affirmation against Lisa’s skin and Dean nods, feeling better now that he knows Lisa and Cas both know he’s straight. 

“If it’s not too forward of me to say so, I’d really like to suck your cock,” Cas says suddenly. He says it exactly the same way people comment on the weather, like it’s perfectly normal for a dude to say that to a guy who just declared he’s straight, and for whatever reason, Dean can’t think of a single thing to say back. Instead, he watches as Cas angles his face towards him as he kisses down Lisa’s chest between her breasts, his hands pushing them up to bury his face between them. Lisa’s rocking underneath Cas, making breathy little sounds, and as Cas mouths his way up one peak to her nipple, Cas flicks his tongue over it while he keeps watching him. “You have the biggest cock I’ve ever seen, and since I’m guessing you’re too straight to fuck me, swallowing your cock while I fuck Lisa would be my second choice.” 

“Second choice huh?” Lisa asks, clearly teasing.

Cas grins down at her, and it’s so _hot_ how he’s so fucking sure of himself even when he’s in another man’s bed and about to—yep, Cas is definitely pushing Lisa’s thighs up and lining himself up between her legs. “Oh,” Cas says, stopping himself before he pushes inside. “Condom?”

“I’m on the pill,” Lisa answers, and before Cas can say anything else, Dean watches her wrap her legs around his lower back and pull him in. He can see the way Cas’s cock sinks into her pussy like it belongs there, and his own hips thrust up into nothing at just how hot it is to see somebody get fucked close up like this. Lisa’s back bows and her tits are put on display in a way that makes his mouth water, and he’s not at all surprised to see Cas lean down to suck her nipple into his mouth. As mesmerized as he is by Cas’s pink lips wrapped around Lisa’s nipple, there’s still one free, so he rolls onto his side to prop himself up with one arm to do the same to her other nipple. 

She moans, nice and loud, and Dean scoots forwards a little bit more so his dick can rub against her leg. He matches the pace Cas sets, moving his body with the back and forth motion of the two of theirs as they fuck, and he tries to focus on how much Lisa is obviously loving this instead of how close his and Cas’s faces are. He’s pretty sure Cas is doing it on purpose when he starts moving closer and closer to where Dean’s lips are currently sucking a mark into Lisa’s soft flesh, but he ignores it because if this is some kind of game of gay chicken, he’s not backing down. 

Dean Winchester never backs down from a challenge, and he’s not afraid of Cas. He’s confused and more turned on by another guy than he thought he ever would be, but he’s not afraid. In fact, to prove just how okay he really is with all of this, he moves his hand between Cas and Lisa to find her clit. He can feel how close she is before he even starts moving his fingers up and down exactly how she likes it. With Cas drilling into her (and the guy isn’t going easy on her, that’s for damn sure) and Dean rubbing her clit just right, it’s inevitable that her orgasm builds quickly.

She gets louder and louder, a sure sign she’s getting close, and like Cas is testing him, he gets closer and closer to Dean’s mouth, too. 

He hears a quiet, breathless, “Shit,” from Lisa as he feels her clit fill rapidly and then throb beneath his fingers, and she calls out as she goes flying into her first orgasm. She catches him completely off-guard when he feels her hand on the back of his head, pushing him until what little space between him and Cas disappears. 

Lisa wants him to kiss Cas. And Cas, well, he sure as hell doesn’t hesitate.

A big, warm hand cups his face. Not gently—more like Cas is holding him in place—and then Cas’s lips crash into his. For the second time tonight, his mind goes blissfully blank. He can think of nothing except the scratch of Cas’s stubble on his face, the firm press of his surprisingly plush lips, and the hot tongue already prodding at his lips. His skin feels like it’s on fucking fire again, his stomach is tight with nerves and arousal, and son of a bitch, does he _want._ Because his brain clearly isn’t working to remind him he doesn’t kiss guys, his mouth opens, and then Cas’s tongue is sweeping into his mouth and he’s being kissed to within an inch of his life.

Cas clearly took Lisa’s advice to heart earlier about how he likes it rough because he dives in hot and fast. Cas’s thumb just beneath his jaw is putting bruising pressure on his tender flesh and drawing a quiet whimper out of him, causing Cas’s teeth to roughly bump and scrape on his lips in his haste to increase the pressure further. He hasn’t kissed anybody but Lisa in years, and it sends an electric current of desire though him when he lets himself enjoy how new this is, how dissimilar it is to kissing Lisa, or hell, any other woman. It’s clear in the way Cas kisses that he’s a man. He’s more firm, obviously stronger than him, and Dean’s cock leaking like a damn tap is letting them all know how fucking into it he is. 

Cas hums against his lips, the low sound seemingly rumbling from his throat straight to Dean’s cock, and he feels what remaining uncertainty he was clinging to melt out of him all at once. He submits completely, turns to putty in Cas’s hands, allowing his head to be guided exactly where Cas wants it. Cas makes a new, pleased sound and his lips press harder against his own. Cas's fingers slide back into his hair and tug to tip his head back. 

This time it’s him who moans as he rides the slippery patch of skin on Lisa’s leg, and Cas takes the opportunity to lick more deeply into his mouth. 

“So hot, babe,” Lisa says.

And that’s when he comes back to himself, wrenching his lips away with his eyes wide and his heart racing.

He’s making out _with a guy._ What the fuck is he doing?

“Don’t you dare chicken out on me now,” Cas rasps, looking like he’s every bit as turned on as Dean is. “Not after that.”

“I-I—”

“Don’t stop!” Lisa complains, which is when he realizes he’s stopped rubbing her clit and Cas has stopped fucking her. He’s about to apologize when he hears Cas give her ass a playful little slap. 

“Hang on a second. I either want to see those lips of his wrapped around my cock, or I need his in my mouth.”

“How do you wanna do it?” Lisa wonders, sounding suddenly interested.

“I’m not putting your dick anywhere near my mouth, dude. I’m not gay,” Dean says for a second time. 

Cas only grins at him. “Well, lucky for you, _I’m_ partially gay, and I’m telling you right now you’re never going to find somebody who wants to suck your cock as much as I do.” Dean shakes his head, too overwhelmed with how his traitorous cock is literally throbbing just from hearing Cas _say_ that. Cas must see how he’s on the fence, because he licks his lips slowly and reveals, “I can deep throat.”

 _“Fuck,”_ Dean whispers, feeling renewed arousal flooding him.

“You love getting head, babe,” Lisa says. “And we both know it’s not my favorite thing to do. I bet he’s good at it, too, listening to what a cock slut he is.” She’s obviously joking, but again, _why is that hot?_ “I think you should go for it.”

“And it’s not gay?” Dean asks, more quietly this time, needing the confirmation from Lisa to go ahead. 

Lisa’s eyes are dancing with laughter. “You are way too obsessed with my tits to be gay, hon.” Dean actually smiles at the truth in that, feeling more comfortable now that it’s confirmed out loud. “You can help him get me off again while Cas gives you a blow job if it’ll make you feel better.”

“Such a selfless sacrifice on your part,” Dean teases. Lisa's smile widens but she raises her eyes in a silent question and he relents with a dramatic sigh. “Fine. If he’s dying for it then whatever. I can just close my eyes and pretend he’s a girl.”

Something flashes in Cas’s eyes at that, but he nods all the same. “Are you into ass play at all?” Cas asks him.

Dean’s face gets so red so fast he wouldn’t be surprised if he lit up the room with it. 

“He loves it,” Lisa answers for him.

He puts one hand over his face and closes his eyes. “I’m just gonna go crawl into a hole and die now.”

“No you’re not,” Cas says firmly. “You’re going to straddle Lisa’s face, facing me. I’m going to suck you down while I fuck Lisa, and Lisa’s going to play with your balls or your ass, whichever she prefers.”

That sounds like an incredibly embarrassing position to be in, and Dean shakes his head. “There’s no way—”

“Come on, baby. Let me see that sexy ass of yours.”

Even though his dick is more than on board with what’s about to go down, he sighs again like he’s not, and says, “Fine. But only for you, Lis.”

It’s more than a little awkward to get himself hovering over Lisa with Cas in the way, and he reluctantly holds onto Cas’s shoulders to steady himself when Cas offers. He’s spared thinking about how muscular Cas’s shoulders are when Lisa’s hands come up to cup his ass, and before he even has time to react to that, Cas leans in and kisses him again. 

Their lips have barely even met when Cas resumes fucking into Lisa, the momentum of each slow thrust taking control of when their lips meet and part over and over. Dean keeps his eyes open so he can look down to where Cas is pistoning his hips and shoving his cock into Lisa again and again as they keep kissing. Cas fucks into Lisa in a powerful thrust that has her calling out, and then he grinds inside of her nice and deep at the same time he licks more deeply into Dean’s mouth. Dean can’t help the whimper that comes out because _fuck_ Cas is good with his tongue. He probably will give good head—and god, that’s a weird (but not unappealing) thought.

“Your lips are sinful,” Cas says between kisses. “You have no idea how many of my boxes you tick, Dean.” 

He’s internally squirming with embarrassment, but that’s when he feels Lisa’s hands spread his ass cheeks and her thumb drags over his hole. 

He lets his head loll back as he says, “God, Lis.” 

He hears a quiet giggle from her that makes him smile, but then he sees Cas lift one eyebrow and his stomach swoops. “Looks like it’s game on.” Cas lowers himself to his elbows and he’s suddenly got a guy inches away from his cock for the first time in his life. His heart is beating so fast he wonders if he’s young enough to have a heart attack. “Hold yourself steady for me, gorgeous.”

For some reason, he follows Cas’s request without even considering the alternative, and he’s absentmindedly stroking himself with Cas’s blue eyes trained on his cock like it’s the holy grail. Nobody has _ever_ looked at him the way Cas looks at him—like he’s the hottest fucking thing Cas has ever seen—and apparently it’s a kink of his because it feels like there’s lava running through his veins the longer it goes on. 

“Stop flirting and fuck me already,” Lisa complains. 

“You never told me how hot he was,” Cas replies, his hot breath ghosting over the head of Dean’s cock. 

“For good reason apparently,” she jokes, and then that’s it. Cas opens his mouth and lowers himself down onto Dean’s cock. 

The wet warmth of a mouth isn’t anything new (though admittedly it’s been a while), but the way Cas moans around him like he’s the best thing he’s ever had in his mouth is, and it’s really fucking hot, too. Lisa traces his hole with her thumb at the same time Cas flicks his eyes up to him while he slowly takes in more and more of his cock and Dean has to grind his teeth together to stop from forcing his cock deeper into his mouth.

 _Son of a bitch,_ Cas looks good with his cock in his mouth. His eyes are darker than they were before, his lips are stretched obscenely around his girth, and with those high cheekbones of his all rosy showing just how aroused he is, Dean couldn’t tear his eyes away from him if he wanted to. Which he really doesn’t. It’s obvious that Cas is loving this and that just makes it that much hotter for him. Heat flashes in Cas’s eyes for a split second, and then Dean sees him get a better grip on Lisa’s thighs, and he starts fucking her again. 

Just like when they were kissing, the intensity of Cas’s thrusts is enough to move his head along with the rest of his body, so each time Cas pitches forwards he takes him into his mouth. Cas starts slow, obviously working himself into a rhythm, and Dean knows he’s comfortable with it when his tongue starts working on his cock in time with his thrusts. At first it’s just pressure on the underside of his cock each time Cas pulls up, but then he starts swirling his tongue around his head and he works his way up to sucking on the tip, and even though he doesn’t have Cas’s full attention, it’s undoubtedly the best blow job he’s ever had.

Lisa is obviously getting fucked well, too, because she keeps forgetting she’s supposed to be playing with his ass, which is actually okay because of how good Cas is swallowing him down. It ends up being a pleasant little bit _extra_ every time she does anything more than squeeze his ass, and when she presses her knuckle firmly against his hole he jerks forwards in surprise and hits the back of Cas’s throat.

When he expected Cas to choke or pull away the way the women he's been with do, Cas only nods his head slightly in a silent okay, and then Dean’s fucking Cas’s face while Cas fucks Lisa and this is officially the hottest he’s ever been. He can feel his orgasm building quickly, making his spine tingle and his stomach swirl with anticipation, and still, he doesn’t stop. He chases his orgasm like a man possessed, completely disregarding everything else except for how good this feels, how good Cas looks sucking his cock, and how desperate he is to spill his load directly into the perfect seal of Cas’s pink lips. 

Like Cas knows how close he is, he redoubles his efforts and starts applying suction each time he pulls up, and _holy fuck_ he’s good at this. Combined with the tongue still sporadically flicking against the underside of his cock and the sounds of skin slapping skin and the wet slurp of the saliva gathering in Cas’s mouth, he’s getting close, and fast. 

“Dean—I need you to—”

Lisa’s voice brings him back to himself enough to look past where Cas has his lips wrapped around him to find Lisa’s pussy. He slides his fingers over her, teasing on either side of her clit, and she groans with pleasure. He watches Cas’s cock pounding into his girlfriend only inches away from his fingers, matching the rhythm of his stroking to the bobbing of Cas’s head, and with the slick heat of Lisa’s cunt on his fingers and the relentless suction and friction on his cock, he can feel his orgasm starting to peak. His muscles are tightening, that familiar but intoxicating sensation is coiling low and boiling hot in his pelvis, and fuck, he’s gonna lose it. He’s gonna come in Cas’s mouth and holy shit it’s gonna feel so good.

“Cas,” Dean croaks, his voice fucking wrecked. 

Cas responds with an enthusiastic moan of his own and the vibration on his cock is driving him to the edge of his orgasm faster than he thought was possible. He feels Lisa’s core tighten, her clit start to get hard against his fingers, and now it’s even hotter knowing that him and Cas are working together to get Lisa off at the same time he’s about to blow his load.

Then Cas does something with his mouth on the next thrust that has him crying out with ecstasy. He feels Cas’s throat opening and _holy fucking shit_ he’s being deep throated for the first time in his entire life and it’s every bit as filthy as he's hoped it would be whenever he jerked off fantasizing about it. His free hand comes up to tangle itself in Cas’s thick hair in a haze of pleasure, and he gets a good grip, pulling slightly to hold Cas in place so he can feel Cas’s throat fluttering around his cock.

“Fuck, Cas,” he breathes, shoving his cock even deeper into Cas’s willing mouth. Cas moans _again,_ and Dean’s gritting his teeth, his whole body as stiff as a board, trying to hold on for a few more seconds of this mind-blowing pleasure. “You’re sucking me so good, Cas. _Oh,_ fuck. I’m so close. I’m gonna—fuck—I’m gonna come so hard for you, baby.” 

He thrusts once, then a second time. He feels Cas swallow around him and the tightening of his throat muscles, and _holy shit_ that feels un-fucking-believable and he’s goddamn _done._ He locks up, seeing stars exploding behind his eyelids as he comes with a strangled shout. He’s coming _hard,_ his whole body convulsing, his cock buried deep in Cas’s throat, and Cas just keeps moaning as he swallows down load after load of Dean’s cum. 

He knows he’s still making sounds—repeating Cas’s name, cursing, praising how good Cas is—but he can’t control himself. He’s petting through Cas’s hair, and his eyes are locked on the arousing sight of Cas’s throat constricting as he swallows down his cum. He breathes out a broken, _“F-fuck,”_ when some clear fluid dribbles from the corner of Cas's mouth because it’s official, he’s never seen anything so erotic in his entire fucking life. If it’s possible, the next spurt of cum shoots out of him even harder, and his head is thrown back with what can only be described as a _howl_ as Cas keeps milking his cock for every last drop. 

Lisa calls out, “Yes, yes, _yes!”_ and his heart skips with surprise—he completely forgot she was even here. Thankfully, he knows she just joined him in his orgasm despite the fact his fingers aren’t moving anymore and he momentarily forgot about her very existence, so he opens his eyes again to check on Cas to see his blue eyes still trained on him.

Dean’s cock slips out of Cas’s mouth, but Cas never looks away from him, his eyes once again staring openly at Dean’s lips. His brain has obviously completely left the building, because between one second and the next, he’s leaning in and smashing his lips to Cas’s. His hand is still in Cas’s hair, and he licks inside of his mouth hungrily, his breath hitching at the taste of his own cum on Cas’s tongue, his cock twitching with an attempt to come back to life already, and _fuck_ Cas is a good kisser.

Cas’s lips fall open and Dean sucks one into his mouth, feels the way Cas’s whole body tenses for about three seconds before he shudders and obviously blows his load inside of Lisa. It’s absolutely stupid, but for a quick second, he feels a pang of jealousy. He wishes it was something _he_ did to make Cas come instead of Lisa, that Cas was as turned on by him as he was by Cas and that he wasn’t the only one who forgot Lisa was here. 

Like Cas can hear his thoughts, he smiles tiredly through his heavy breathing and says, “Your fucking mouth, Dean.”

Dean’s pleased on a level he didn’t even know he could be, and now that there’s no reason to stay up on his knees, he carefully disentangles himself from both Cas and Lisa and flops flat on his back onto the bed, still breathing hard, waiting for the circulation to work itself into his legs and for his ears to stop ringing. 

_God,_ he can’t believe he did any of that. He can’t believe how fucking hot it was. A tiny part of him feels like it was wrong to get off from a guy like that when he’s not gay, but it was _so good_ he can’t find it in him to care right now. Hell, he sorta wants to do it over and over again. When’s the last time he came that hard? That he was _that_ into sex? And it wasn’t even actual sex! He can’t even remember... doesn’t know if it’s ever happened? Holy fuck, that could’ve been the best sex of his whole damn life! 

He hums quietly when he feels Lisa’s fingers in his hair, and turns his head her way to aim a satisfied smile in her direction. There’s fondness in her eyes, but something more penetrating, too.

“What?” he asks quietly.

Her lips curve into a smile. “Enjoy yourself?”

“Wasn’t it obvious?” he laughs.

“Oh, it was obvious. Sounds like I’m gonna have to get some tips from Cas here on deep throating because we’ve been together for two years and I’ve never heard you yell like that for me.”

He feels self-conscious when he flicks his eyes over to find Cas for help, only to see him already in boxers and pulling up his pants. 

“I’ll take that as a compliment,” Cas says, smiling first at Lisa, and then at him. The second their eyes catch Dean feels arousal and guilt warring in his stomach.

“You don’t have to leave right away,” Lisa tells him. “You can at least catch your breath first.”

“Unfortunately, I have a plane to catch in a few hours,” Cas says.

Lisa pushes herself up to her elbows. “You’re leaving today?”

“Yes,” Cas nods. Dean can’t stop watching him as he pulls his shirt on and starts doing up the buttons. As hot as he is with no shirt on, it’s still sexy as hell to see him putting himself together again, slowly turning back into the nerd he was when he walked in here. “Unfortunate timing on my part. I really would’ve enjoyed staying for a second round.”

“Oh. I don’t know that we were into it enough to do this again,” Lisa says, looking at Dean for confirmation. He feels disappointment sweep through him, but can’t exactly blame her considering how everything went down tonight. “Turns out I don’t like sharing my man as much as I thought I would.”

Dean wonders if Cas picked up on the possessiveness in _my man_ the same way he did, or if he only hears it because of how well he knows Lisa. 

“Completely understandable,” Cas says. He sits on the foot of the bed to put his socks on, and looks over his shoulder at Dean when he asks, “I hope I didn’t cross any boundaries?”

Dean is hyper-aware of Lisa watching him for his response. He can’t help the blush that heats his cheeks, but he shakes his head. “No complaints from me.”

Cas smiles, a small, soft smile that he hasn’t seen from him before, and it does nothing to help how hot his face is. 

“Do you need me to walk you out or can we get started on round two without you?” Lisa asks, sliding her hand up Dean’s chest pointedly. 

Cas starts to say, “I can walk myself—”

But Dean interrupts, with, “Don’t be stupid. I’ll walk you out, man.” He leans over to peck Lisa on the lips and quickly searches out his boxers and his t-shirt while Cas says goodbye to Lisa.

“I’ll give you a call when I come back,” Cas says.

“You’ll have forgotten all about me in five years,” Lisa flirts.

“I doubt that very much,” Cas says sincerely. “You were amazing, Lisa. Take care of yourself.”

Then Dean follows Cas down the hallway, feeling something like nerves twisting up his insides that makes the tiny hairs on the back of his neck stand up. They reach the door without a single word said between them, and then Cas turns to face him with his hands in his pockets, and the second he’s hit with those blue eyes again he feels his heart rate pick up. 

Cas’s words feel careful when he says, “This was fun.”

Dean licks his lips nervously and nods his head. “Bit of an eye-opener.”

There’s a hint of mischief in Cas’s smile when it appears again, and his voice is a little bit deeper than it was a second ago. “I’ll take that as a compliment, too.” _Fuck._ Is he flirting or is Dean reading too much into this? “I really do wish I could stay.”

His heart is certainly getting a work out today as it starts galloping again. His palms are sweating and his throat is as dry as a desert. “Probably not a good idea anyway. I’m already never gonna hear the end of being noisier with you.”

“And to think that was while I was distracted,” Cas reminds him, planting the seed of how good he could be if it was just the two of them as Cas's eyes sweep up and down his body greedily. “Let me know if Lisa changes her mind in the next five years. I’d definitely be open to doing this again if you’re included.”

Without meaning to or even knowing what he’s doing, he drifts closer to Cas, the little bit of space between them charged with mutual attraction so thick he can hardly breathe through it. “I’ll start working on her tomorrow,” he says quietly, drawing a husky chuckle from Cas he’s sure he’ll be repeating in his head for years to come.

Cas reaches out to slowly drag his thumb over Dean’s bottom lip, completely stealing his breath and causing him to stand there without breathing. 

“Do me a favor and think hard about the whole ‘I’m straight’ thing when I’m gone. Maybe that way when I spend the next five years dreaming about really putting your lips to work, it won’t be for nothing.” Dean’s breath comes out in a laugh despite his flaming cheeks, and with one final smile, Cas’s palm trails down to Dean’s arm, stopping for one second too long when his fingers slip into his hand for a quick squeeze, and then he opens the door and walks through it. 

He watches Cas from the doorway as he makes his way down their sidewalk and into a truly awful, ancient Toyota Corolla, feeling oddly empty when he drives away. 

He shakes it off the best he can on the way back to Lisa in their bedroom, and he’s more than willing to let her familiar mouth and soft curves distract him. When he comes for the second time that night buried deep inside of his girlfriend secretly wishing it was Cas pinning him to the bed instead of her, he figures nobody has to know about that but him.  
  
Unfortunately, once Lisa falls asleep next to him, there's nothing to tear his thoughts away from the confusion he still has swirling in his mind about the blue-eyed man who just walked into his house and changed everything he thought he knew about himself. It takes him forever to fall asleep that night, but when he finally does, he's completely oblivious to the life-changing ramifications tonight will end up having...

**Author's Note:**

> This is the beginning of a new story I'm working on. I decided to post it as a stand-alone fic so that readers who don't like reading Dean/Cas/Others can skip it and still read the main story (which is only Dean/Cas from here on). I probably won't be posting the next part of the series for a little while since I'm working on my DCBB now, but this was done and I was dying to get it out there, so I hope you enjoyed it!
> 
> As usual, the title is shamelessly stolen from Taylor Swift ;)


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